Sodium Iodide → 2-(2-Hydroxyisobutyl)-Phthalimide

HRID 229940

반응식

HRID 229940 반응식
Cl[CH2:2][C:3]([CH3:6])([OH:5])[CH3:4].[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.[K].[I-].[Na+]>CN(C=O)C>[OH:5][C:3]([CH3:6])([CH3:4])[CH2:2][C:9]12[CH:13]=[CH:14][CH:15]=[CH:16][CH:8]1[C:7]([NH:11][C:10]2=[O:12])=[O:17]

참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 684091-Chloro-2-methylpropan-2-olHCID 24194345Phthalimide potassium salt

생성물 1

HCID 685388332-(2-Hydroxyisobutyl)-Phthalimide수율 37%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1-chloro-2-methyl-2-propanol (2.23 g, 97%, 0.02 mol), potassium phthalimide (3.780 g, 98%, 0.02 mol) and sodium iodide (60 mg, 4 mmol) in anhydrous DMF (40 mL) was heated to reflux overnight. The solvent was evaporated under reduced pressure. The resulting product was triturated with a mixture of 3:2 ethyl acetate/hexanes and the ensuing white precipitate was removed by filtration. The yellow filtrate was concentrated under reduced pressure and purified by flash chromatography in a mixture of 2:3 ethyl acetate/hexanes. The impure product thus isolated was triturated with hot hexanes (125 mL) and filtered to remove an insoluble white impurity. After evaporation of the solvent under reduced pressure, the obtained white solid was recrystallized in hexanes. The product was yielded as colorless crystals that were collected by filtration and dried under high vacuum (1.63 g, 37% yield). m.p.: 104-105° C.; TLC Rf 0.20 (2:3 ethyl acetate/hexanes); FTIR (KBr): 3524, 3456, 3097, 3031, 2973, 2930, 1773, 1698, 1611, 1466, 1427, 1389, 1319, 1190, 1076, 990, 965, 912, 890, 838, 766, 724, 712, 638 cm−1; 1H-NMR(500 MHz, CDCl3): δ 1.26 (s, 6H, 2 CH3), 2.74 (s, 1H, OH), 3.75 (s, 2H, CH2), 7.72 (dd, 2H, Jo=5.44 Hz, Jm=3.04 Hz, 2 Hc), 7.85 (dd, 2H, Jo=5.42 Hz, Jm=3.06 Hz, 2 Hb); 13C-NMR(126 MHz, CDCl3): δ 27.6 (2 CH3), 49.3 (CH2), 71.6 (CMe2), 123.6 (2 Cb), 132.0 (2 Ca), 134.3 (2 Cc), 169.3 (2 CO).

후처리

  1. temperatureto reflux overnight
  2. customThe solvent was evaporated under reduced pressure
  3. customThe resulting product was triturated with a mixture of 3:2 ethyl acetate/hexanes
  4. customthe ensuing white precipitate was removed by filtration
  5. concentrationThe yellow filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography in a mixture of 2:3 ethyl acetate/hexanes
  7. customThe impure product thus isolated
  8. customwas triturated with hot hexanes (125 mL)
  9. filtrationfiltered
  10. customto remove an insoluble white impurity
  11. customAfter evaporation of the solvent under reduced pressure
  12. customthe obtained white solid was recrystallized in hexanes
  13. customThe product was yielded as colorless crystals that
  14. filtrationwere collected by filtration
  15. customdried under high vacuum (1.63 g, 37% yield)

출처 및 근거

ORD 기록
ord-bbcac84b16404f4cbedecc6335780fc3
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563920B2

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